JP3679656B2 - 新規マクロライド誘導体 - Google Patents

新規マクロライド誘導体 Download PDF

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Publication number: JP3679656B2
Authority: JP; Japan
Prior art keywords: formula; alkyl; compound; aryl; compounds
Prior art date: 1998-10-09
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

JP28683599A

Other languages

English (en)

Japanese (ja)

Other versions

JP2000119294A (ja

Inventor

ブライアン・スコット・ブロンク

ヘンミャオ・チェン

ジェイソン・ケネス・デュートラ

マイケル・アンソニー・レタヴィック

ロバート・ジョン・ラフカ

Original Assignee

ファイザー・プロダクツ・インク

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-10-09

Filing date

1999-10-07

Publication date

2005-08-03

1999-10-07 Application filed by ファイザー・プロダクツ・インク filed Critical ファイザー・プロダクツ・インク

2000-04-25 Publication of JP2000119294A publication Critical patent/JP2000119294A/ja

2005-08-03 Application granted granted Critical

2005-08-03 Publication of JP3679656B2 publication Critical patent/JP3679656B2/ja

2019-10-07 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000003120 macrolide antibiotic agent Substances 0.000 title description 15
150000001875 compounds Chemical class 0.000 claims description 186
150000003839 salts Chemical class 0.000 claims description 43
-1 3-quinolinyl Chemical group 0.000 claims description 39
238000000034 method Methods 0.000 claims description 20
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
238000010168 coupling process Methods 0.000 claims description 15
238000005859 coupling reaction Methods 0.000 claims description 15
239000003153 chemical reaction reagent Substances 0.000 claims description 13
230000008878 coupling Effects 0.000 claims description 11
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 10
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
SLGVJLNVPYQNNK-UHFFFAOYSA-N 3h-cinnolin-4-one Chemical compound C1=CC=C2C(=O)CN=NC2=C1 SLGVJLNVPYQNNK-UHFFFAOYSA-N 0.000 claims description 9
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 9
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 9
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 3
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical group Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 3
125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 82
125000003118 aryl group Chemical group 0.000 description 74
125000002887 hydroxy group Chemical group [H]O* 0.000 description 64
125000000217 alkyl group Chemical group 0.000 description 57
125000005843 halogen group Chemical group 0.000 description 56
125000001424 substituent group Chemical group 0.000 description 46
125000004093 cyano group Chemical group *C#N 0.000 description 44
125000001072 heteroaryl group Chemical group 0.000 description 44
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 44
208000015181 infectious disease Diseases 0.000 description 42
150000001540 azides Chemical class 0.000 description 41
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 39
125000003342 alkenyl group Chemical group 0.000 description 37
125000000304 alkynyl group Chemical group 0.000 description 37
238000012360 testing method Methods 0.000 description 33
229920006395 saturated elastomer Polymers 0.000 description 29
125000002877 alkyl aryl group Chemical group 0.000 description 19
241001465754 Metazoa Species 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
238000011282 treatment Methods 0.000 description 17
125000000623 heterocyclic group Chemical group 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
230000001580 bacterial effect Effects 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
241000251468 Actinopterygii Species 0.000 description 13
208000035143 Bacterial infection Diseases 0.000 description 13
241000124008 Mammalia Species 0.000 description 13
208000022362 bacterial infectious disease Diseases 0.000 description 13
239000000243 solution Substances 0.000 description 13
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
241000699670 Mus sp. Species 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
239000000203 mixture Substances 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
229910052760 oxygen Inorganic materials 0.000 description 11
229910052717 sulfur Inorganic materials 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
241000283690 Bos taurus Species 0.000 description 10
239000002253 acid Substances 0.000 description 10
230000000694 effects Effects 0.000 description 10
238000002474 experimental method Methods 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 9
241000271566 Aves Species 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
238000003556 assay Methods 0.000 description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
206010037075 Protozoal infections Diseases 0.000 description 7
125000004122 cyclic group Chemical group 0.000 description 7
201000010099 disease Diseases 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 7
239000011734 sodium Substances 0.000 description 7
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 6
229940079593 drug Drugs 0.000 description 6
239000003814 drug Substances 0.000 description 6
235000019439 ethyl acetate Nutrition 0.000 description 6
125000005842 heteroatom Chemical group 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
210000003491 skin Anatomy 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000007920 subcutaneous administration Methods 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
0 C=*C1OCCN1N Chemical compound C=*C1OCCN1N 0.000 description 5
241000699666 Mus <mouse, genus> Species 0.000 description 5
241000191967 Staphylococcus aureus Species 0.000 description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
150000001299 aldehydes Chemical class 0.000 description 5
125000004183 alkoxy alkyl group Chemical group 0.000 description 5
125000006350 alkyl thio alkyl group Chemical group 0.000 description 5
125000004414 alkyl thio group Chemical group 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 5
239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000010790 dilution Methods 0.000 description 5
239000012895 dilution Substances 0.000 description 5
230000002949 hemolytic effect Effects 0.000 description 5
229940041033 macrolides Drugs 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000011593 sulfur Substances 0.000 description 5
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
229920001817 Agar Polymers 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 4
241000588724 Escherichia coli Species 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
241000588652 Neisseria gonorrhoeae Species 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000008272 agar Substances 0.000 description 4
125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
239000012267 brine Substances 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
239000003937 drug carrier Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
150000007522 mineralic acids Chemical class 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
238000003752 polymerase chain reaction Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
230000008261 resistance mechanism Effects 0.000 description 4
238000007665 sagging Methods 0.000 description 4
238000013207 serial dilution Methods 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
241000894006 Bacteria Species 0.000 description 3
241000193403 Clostridium Species 0.000 description 3
241000606768 Haemophilus influenzae Species 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
208000010362 Protozoan Infections Diseases 0.000 description 3
210000000683 abdominal cavity Anatomy 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
238000003113 dilution method Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
239000012458 free base Substances 0.000 description 3
229940047650 haemophilus influenzae Drugs 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
231100000225 lethality Toxicity 0.000 description 3
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210000005075 mammary gland Anatomy 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
241000894007 species Species 0.000 description 3
125000000335 thiazolyl group Chemical group 0.000 description 3
WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
241001647372 Chlamydia pneumoniae Species 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
241000194033 Enterococcus Species 0.000 description 2
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
241000590002 Helicobacter pylori Species 0.000 description 2
241000282412 Homo Species 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
241001529936 Murinae Species 0.000 description 2
241000186364 Mycobacterium intracellulare Species 0.000 description 2
GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
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206010035664 Pneumonia Diseases 0.000 description 2
229920000954 Polyglycolide Polymers 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
206010062255 Soft tissue infection Diseases 0.000 description 2
241000295644 Staphylococcaceae Species 0.000 description 2
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241000193985 Streptococcus agalactiae Species 0.000 description 2
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241000193996 Streptococcus pyogenes Species 0.000 description 2
241001312524 Streptococcus viridans Species 0.000 description 2
206010048762 Tooth infection Diseases 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
230000000845 anti-microbial effect Effects 0.000 description 2
238000011203 antimicrobial therapy Methods 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
125000002393 azetidinyl group Chemical group 0.000 description 2
IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 2
229960004099 azithromycin Drugs 0.000 description 2
MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 2
244000052616 bacterial pathogen Species 0.000 description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
210000004556 brain Anatomy 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
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150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
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125000001309 chloro group Chemical group Cl* 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
230000001332 colony forming effect Effects 0.000 description 2
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238000007796 conventional method Methods 0.000 description 2
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ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
208000004396 mastitis Diseases 0.000 description 2
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229910052763 palladium Inorganic materials 0.000 description 2
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NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
229920000747 poly(lactic acid) Polymers 0.000 description 2
239000004633 polyglycolic acid Substances 0.000 description 2
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239000001267 polyvinylpyrrolidone Substances 0.000 description 2
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235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
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230000002265 prevention Effects 0.000 description 2
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208000023504 respiratory system disease Diseases 0.000 description 2
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239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
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239000007858 starting material Substances 0.000 description 2
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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239000000312 peanut oil Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000002953 phosphate buffered saline Substances 0.000 description 1
150000008105 phosphatidylcholines Chemical class 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
230000026731 phosphorylation Effects 0.000 description 1
238000006366 phosphorylation reaction Methods 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
229920001610 polycaprolactone Polymers 0.000 description 1
229920002721 polycyanoacrylate Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000656 polylysine Polymers 0.000 description 1
229920006324 polyoxymethylene Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
YGXCETJZBDTKRY-DZCVGBHJSA-N pristinamycin IA Chemical compound N([C@@H]1C(=O)N[C@@H](C(N2CCC[C@H]2C(=O)N(C)[C@@H](CC=2C=CC(=CC=2)N(C)C)C(=O)N2CCC(=O)C[C@H]2C(=O)N[C@H](C(=O)O[C@@H]1C)C=1C=CC=CC=1)=O)CC)C(=O)C1=NC=CC=C1O YGXCETJZBDTKRY-DZCVGBHJSA-N 0.000 description 1
239000000047 product Substances 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
208000028172 protozoa infectious disease Diseases 0.000 description 1
244000079416 protozoan pathogen Species 0.000 description 1
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000011002 quantification Methods 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
230000003252 repetitive effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
208000020029 respiratory tract infectious disease Diseases 0.000 description 1
230000004044 response Effects 0.000 description 1
201000003068 rheumatic fever Diseases 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000012216 screening Methods 0.000 description 1
238000012163 sequencing technique Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
201000009890 sinusitis Diseases 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000011083 sodium citrates Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
208000000995 spontaneous abortion Diseases 0.000 description 1
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229940041030 streptogramins Drugs 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
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235000020357 syrup Nutrition 0.000 description 1
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230000009885 systemic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000002053 thietanyl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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206010044325 trachoma Diseases 0.000 description 1
108091005703 transmembrane proteins Proteins 0.000 description 1
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231100000397 ulcer Toxicity 0.000 description 1
208000000143 urethritis Diseases 0.000 description 1
210000001635 urinary tract Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

JP28683599A 1998-10-09 1999-10-07 新規マクロライド誘導体 Expired - Fee Related JP3679656B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US10383898P	1998-10-09	1998-10-09
US60/103838		1998-10-09

Publications (2)

Publication Number	Publication Date
JP2000119294A JP2000119294A (ja)	2000-04-25
JP3679656B2 true JP3679656B2 (ja)	2005-08-03

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JP28683599A Expired - Fee Related JP3679656B2 (ja)	1998-10-09	1999-10-07	新規マクロライド誘導体

Country Status (10)

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US (1)	US6100240A (de)
EP (1)	EP0992509B1 (de)
JP (1)	JP3679656B2 (de)
AT (1)	ATE277062T1 (de)
BR (1)	BR9905089A (de)
CA (1)	CA2286511C (de)
DE (1)	DE69920362T2 (de)
DK (1)	DK0992509T3 (de)
ES (1)	ES2226294T3 (de)
PT (1)	PT992509E (de)

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ES2281136T3 (es) *	1997-09-10	2007-09-16	Merial Ltd.	Uso de 9a-azalidos como agentes antimicrobiales veterinarios.
US6339063B1 (en)	1997-09-10	2002-01-15	Merck & Co., Inc.	9a-azalides as veterinary antimicrobial agents
EP1779853A3 (de) *	1997-09-10	2010-01-27	Merial Ltd.	9a-Azalide als antimikrobielle Wirkstoffe für die Veterinärmedizin
AP9801420A0 (en) *	1998-01-02	1998-12-31	Pfizer Prod Inc	Novel macrolides.
AP1060A (en) *	1998-01-02	2002-04-23	Pfizer Prod Inc	Novel erythromycin derivatives.
CA2359708C (en) *	1999-01-27	2005-10-25	Pfizer Products Inc.	Ketolide antibiotics
CA2411293A1 (en) *	1999-01-28	2000-07-28	Pfizer Products Inc.	Novel azalides and methods of making same
US6939861B2 (en)	1999-04-16	2005-09-06	Kosan Biosciences, Inc.	Amido macrolides
HUP0201516A3 (en) *	1999-05-24	2003-03-28	Pfizer Prod Inc	13-methyl-erythromycin derivatives, process for their preparation and pharmaceutical compositions containing them
US6420535B1 (en) *	1999-06-07	2002-07-16	Abbott Laboratories	6-O-carbamate ketolide derivatives
BR0110382A (pt) *	2000-04-27	2003-06-24	Pfizer Prod Inc	Utilização de composições antibióticas azalida para o tratamento ou prevenção de uma infecção causada por bactérias ou protozoários em mamìferos
JP2005538927A (ja) *	2002-01-17	2005-12-22	コーザンバイオサイエンシスインコーポレイテッド	アミドマクロライド
EP1483579A4 (de)	2002-02-15	2006-07-12	Merckle Gmbh	Konjugate biologisch aktiver verbindungen, verfahren zu ihrer herstellung und verwendung, formulierung und pharmazeutische anwendungen davon
AU2003219770B2 (en)	2002-02-15	2008-10-09	Merckle Gmbh	Conjugates of biologically active compounds, methods for their preparation and use, formulation and pharmaceutical applications thereof
US7271154B2 (en)	2002-02-15	2007-09-18	Merckle Gmbh	Antibiotic conjugates
CN101423539B (zh) *	2008-12-09	2011-04-27	山东大学	4″,11-二氨基甲酸酯阿奇霉素衍生物、制备方法及其药物组合物
CN103965273B (zh) *	2013-08-23	2016-05-25	普莱柯生物工程股份有限公司	一种大环内酯类化合物
CN105669798B (zh) *	2013-08-23	2019-07-26	普莱柯生物工程股份有限公司	一种大环内酯类化合物
CN109535211B (zh) *	2018-12-19	2020-05-08	江苏威凌生化科技有限公司	一种合成纯化泰拉霉素杂质c的方法

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US5441939A (en) *	1994-03-04	1995-08-15	Pfizer Inc.	3"-desmethoxy derivatives of erythromycin and azithromycin
US5641753A (en) *	1996-03-25	1997-06-24	Chris E. Platt	10-AZA-9-deoxo-11-deoxy-erythromycin A and derivatives combined with sulfisoxazole
HN1998000086A (es) *	1997-06-11	1999-03-08	Pfizer Prod Inc	Derivados de 9 - desofo - 9 aza - 9a - homoeritromicina a - c - 4 sustituidos.
HN1998000074A (es) *	1997-06-11	1999-01-08	Pfizer Prod Inc	Derivados de macrolidos c-4 sustituidos

1999
- 1999-09-16 US US09/396,876 patent/US6100240A/en not_active Expired - Fee Related
- 1999-10-07 CA CA002286511A patent/CA2286511C/en not_active Expired - Fee Related
- 1999-10-07 JP JP28683599A patent/JP3679656B2/ja not_active Expired - Fee Related
- 1999-10-08 PT PT99307938T patent/PT992509E/pt unknown
- 1999-10-08 DE DE69920362T patent/DE69920362T2/de not_active Expired - Fee Related
- 1999-10-08 ES ES99307938T patent/ES2226294T3/es not_active Expired - Lifetime
- 1999-10-08 EP EP99307938A patent/EP0992509B1/de not_active Expired - Lifetime
- 1999-10-08 AT AT99307938T patent/ATE277062T1/de not_active IP Right Cessation
- 1999-10-08 DK DK99307938T patent/DK0992509T3/da active
- 1999-10-11 BR BR9905089-7A patent/BR9905089A/pt not_active Application Discontinuation

Also Published As

Publication number	Publication date
US6100240A (en)	2000-08-08
JP2000119294A (ja)	2000-04-25
DE69920362T2 (de)	2006-02-09
EP0992509A3 (de)	2001-03-07
BR9905089A (pt)	2000-08-08
ES2226294T3 (es)	2005-03-16
ATE277062T1 (de)	2004-10-15
DE69920362D1 (de)	2004-10-28
EP0992509B1 (de)	2004-09-22
CA2286511C (en)	2003-07-08
CA2286511A1 (en)	2000-04-09
EP0992509A2 (de)	2000-04-12
PT992509E (pt)	2004-12-31
DK0992509T3 (da)	2004-12-20

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Publication	Publication Date	Title
JP3679656B2 (ja)	2005-08-03	新規マクロライド誘導体
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JP3947360B2 (ja)	2007-07-18	ケトリド抗生物質
US6664238B1 (en)	2003-12-16	Carbamate and carbazate ketolide antibiotics
KR20010033822A (ko)	2001-04-25	신규 에리트로마이신 유도체
EP1132392B1 (de)	2004-03-03	Ketolidantibiotika
EP0984019B1 (de)	2004-06-02	C11-Carbamate von antibakteriellen Makroliden
JP2002528553A (ja)	2002-09-03	新規なマクロライド抗生物質
US6291656B1 (en)	2001-09-18	Tricyclic erythromycin derivatives
US6727352B2 (en)	2004-04-27	Methods of making macrolides
US6262030B1 (en)	2001-07-17	Erythromycin derivatives
EP1114826A2 (de)	2001-07-11	Antibakterielle und prokinetische Makroliden
EP1167376B1 (de)	2004-07-14	Makrolid-Antibiotika
JP2001348397A (ja)	2001-12-18	エリスロマイシンａ誘導体
JP2001213893A (ja)	2001-08-07	新規な１３及び１４員抗菌及びプロカイネティックマクロライド並びにこれらの中間体
US20020061856A1 (en)	2002-05-23	Novel tricyclic erythromycin derivatives
EP1115732B1 (de)	2005-06-29	Carbamat- und carbazatketolidantibiotika
US20020077302A1 (en)	2002-06-20	Tricyclic erythromycin derivatives
EP1298138B1 (de)	2006-11-02	Carbamat und Carbazat Ketolid Antibiotika
MXPA99009269A (en)	2000-10-01	New derivatives of macroli
MXPA01002355A (en)	2002-06-05	Ketolide antibiotics
MXPA00011389A (en)	2002-06-05	New macrolide
EP1749832A2 (de)	2007-02-07	Carbamat und Carbazat Ketolid Antibiotika
MXPA99007717A (en)	2000-06-05	Carbamates c11 of antibacterials macroli